Quantifying the Reactivity of a Remarkably Long-Lived Difluorinated Enol in Acidic Methanol via Solution Kinetics and Electronic Structure Calculations

A simple enol acetal underwent rapid cleavage in acidic solution to generate a difluorinated enol, which
was sufficiently long-lived to be characterized by 2D NMR in a protic solvent at ambient temperature.
Density functional theory calculations on a model reaction suggest that there are significant differences
in protonation transition state timing between the fluorinated and nonfluorinated enols.